Transportation industries (e.g., airlines) often operate under regulatory guidelines related to, among others, flight and duty time limitations, rest requirements, fitness for duty requirements, and the like. These guidelines can vary over time. On one hand, compliance with updated guidelines may be achieved with revisions to staffing approaches, flight schedules, and/or the like. On the other hand, such revisions can be time-consuming, lead to reduced revenue, increased staffing expenses, and otherwise present organizational challenges. Accordingly, improved approaches for operating in accordance with regulatory guidelines (e.g., Federal Aviation Regulations and/or the like) remain desirable.